When Leslie Ann Woodward describes her life, she does so with the calm confidence of someone who has already lived several lives in one. She has been a teenage fast food worker in a Virginia mall, a breakout Elite model in Europe, a favorite of Versace, a marketing strategist for one of the greatest athletes in history, a skincare innovator in Beverly Hills, and a designer with a knack for breathing new life into old Hollywood estates. And woven through the forward momentum of her career are the friendships and social circles that shaped some of the most interesting chapters of her story, including a role she never expected: helping Donald Trump assess the woman who would become Melania Trump.
Today, Woodward’s path reflects an unusual blend of glamour, reinvention, and resilience, the kind of non-linear trajectory that modern entrepreneurs admire for its flexibility and range. But her ability to shift industries and remain relevant across decades has roots in a work ethic formed much earlier.
From Chick- fil -A to the Cosby Show
Woodward grew up in Fredericksburg, Virginia, and entered the workforce early. At twelve, she was already clocking shifts at a Chick-fil-A in Spotsylvania Mall. At fifteen, she created what would later become known to customers as THE Chick-fil-A Sauce, working under her manager, Hugh Fleming. The recipe’s adoption would become a local point of pride, and for Woodward, a sign that she could spot consumer appeal long before she knew what brand strategy was.
After graduating from James Monroe High School in 1986, she headed to New York City and signed with Elite Model Management under John Casablancas. Acting work on The Cosby Show earned her a SAG card, and Bill Cosby granted her a hometown press cover story that introduced her career to the public. She was still a teenager.
A European Breakout
Her ascent accelerated once she moved to Europe. Gianni Versace became an early supporter, inviting her to walk a headline-making show on the Spanish Steps in Rome. The dramatic backdrop and bold styling helped transform Woodward into an international name. Work with Valentino, Gianfranco Ferré, Fendi, Chloe, and Thierry Mugler followed. Magazine covers in Germany and France kept her in high demand, and television spots for Levi’s, Diet Coke, and other global brands made her a familiar face.
By the mid-1990s, she was one of Elite’s top earners, appearing in campaigns that defined a generation of fashion advertising.
Reinventing Herself in Business
At a moment when many models would coast on past success, Woodward shifted. She joined Steffi Graf GmbH as the United States marketing director, where she produced a critically praised charity calendar for the World Wildlife Fund. Her pitch to Sports Illustrated editor Jule Campbell to include female athletes in the swimsuit edition helped lay the groundwork for a new chapter in the magazine’s evolution. Graf became the first, a milestone later highlighted in the documentary Beyond the Gaze.
Her transition into the medical and skincare world came in 2004, when she began working with Beverly Hills physicians Dr Douglas Hamilton and Dr Babak Azizzadeh. She co-created the skincare line DEEP and contributed to the beauty reference book Beverly Hills Beauty Secrets, merging her industry knowledge with scientific insight.
Design soon followed. After marrying producer Robert Evans, she redesigned their home, known as Woodland. Architectural Digest placed the renovation on its cover, cementing Woodward’s standing not only as a former model with style but as a creative with vision and execution.
Inside the Trump Social Orbit
If Woodward’s professional résumé reads like a tour through several industries, her social one reflects the particular glamour of the late twentieth-century international set. In the early 1990s, she lived in Europe and dated Italian businessman Marco Savi. Through him, she met Roffredo Gaetani, who at the time was romantically involved with Ivana Trump. Italian men often traveled and socialized in groups, and Woodward soon found herself part of a lively network that included both Gaetani and Ivana.
Ivana made an immediate impression. “She was a force, and I admired her,” Woodward recalls. Their friendship grew, and with it came a window into the unique dynamic between Ivana and her former husband. Despite being divorced, they were still a social unit. “If Ivana was invited to something, Donald came. If Donald was invited to something, Ivana came. I found their relationship incredibly interesting, mature and evolved.”
Through this circle, Woodward became acquainted with Donald Trump. After her relationship with Savi ended, Trump began reaching out more often. Accounts from friends who teased him that he would never win over Woodward reportedly heightened his interest. But she never viewed him romantically. Their connection was rooted in mutual respect. “As busy as he was, I could get Donald on the phone at any time. He always took my call,” she says. When she went on dates, he sometimes offered unsolicited but friendly commentary to the men sitting across from her, usually along the lines of “treat this one well” or “you are lucky.”She viewed him more as an ally than a suitor.
Then came the dinner that would unexpectedly shape the future of the Trump family.
The Night Donald Trump Introduced Her to Melania
In 1998, Trump called Woodward and asked her to join him for dinner. He said he wanted her opinion of a woman he had recently met through Paolo Zampolli. That woman was Melania Knauss.
Woodward accepted because she believed he genuinely valued her perspective. Only later did she consider that he might have had a different strategy in mind. “Looking back, I am pretty sure he was hedging his bets. Bring two women to dinner, and they will both see you as a catch and compete. That kind of thing.” But the evening did not unfold that way.
Instead of rivalry, Woodward and Melania connected. Woodward found her poised, thoughtful, and well-suited for Trump’s lifestyle. Melania found it both surprising and refreshing that Trump wanted another woman’s honest opinion. Instead of competition, there was mutual recognition.”He underestimated Melania and me,” Woodward reflects. “We both appreciated each other’s position. I thought she was perfect for him.”
It was, in its own way, a quiet but pivotal endorsement at a moment when their relationship was still forming.
The Later Chapters
She became a mother in 2015, and her worldly experience became a pool of wisdom to pour into her greatest blessing and creation – her daughter.
Today, she stands as a rare example of someone who moved fluidly between fashion, business, beauty, design, and cultural circles spanning continents. Her story is not linear, but it is distinctly modern. It is the profile of a woman who has never stopped learning, never stopped reinventing, and never stopped moving.
Look for her story coming to print and screen soon.
